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Siesta Isles Real Estate Sold55+ Active AdultNo HOA

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Siesta Isles, 18308 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Sold - Aug 29, 2025
$730,000 $135K
  • 3 Beds
  • 3 Baths
  • 2,122 SqFt
  • $344/SqFt
House sold in Siesta Isles
18308 Cutlass Dr, Fort Myers Beach, FL 33931
Discover your dream waterfront home in fort myers beach! Seize the opportunity to finish building your dream waterfront home in the exclusive siesta isles community of fort myers beach, where luxury meets coastal living. This extraordinary property is perfectly situated to cater to boating enthusiasts and families alike, nestled in one of the best boating communities in the area, offering direct sailboat access to the open waters. Experience the thrill of customizing your home to reflect your personal taste and style. The possibilities are endless, allowing you to design a space that meets your every desire. Whether you envision an expansive open-concept living area, a gourmet kitchen, or serene bedrooms with sweeping water views, the canvas is yours to create. Step outside to discover an outdoor oasis designed for entertaining. The covered patio invites you to relax in the shade or host vibrant gatherings, while the private swimming pool offers a cool retreat on warm sunny days. Imagine making unforgettable memories as you bask in the sun or enjoy a tranquil evening by the water. For those who cherish life on the water, this property features a private slip spacious deep-water access canal, capable of accommodating large boats. Embrace the boating lifestyle and set sail into the sparkling waters of southwest florida, where adventure awaits at every turn. Indulge in fishing, water sports, or leisurely boat rides as you explore the stunning coastal landscapes of the gulf of mexico. This idyllic setting promises a peaceful retreat from the hustle and bustle of everyday life, allowing you to unwind and rejuvenate in the comfort of your own home. Just minutes away from fort myers beach, you'll have convenient access to pristine white sandy beaches and vibrant coastal communities, including the renowned sanibel and captiva islands. One of the standout features of this property is that there is no homeowners association (hoa), granting you the freedom to enjoy your property without restrictions. Whether you're an avid boater or simply appreciate the beauty and serenity of waterfront living, this estate offers the ultimate lifestyle for those who cherish the ocean. With the option to build out your custom home, this is not just a property; it is an invitation to a life of luxury and leisure. Option available to complete your paradise dream home with the seller. Begin a new chapter in your life and embrace all the beauty and adventure that come with this exceptional waterfront estate in fort myers beach!
Siesta Isles, 18307 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Sold - Jul 31, 2025
$820,000 $155K
  • 3 Beds
  • 3 Baths
  • 2,452 SqFt
  • $334/SqFt
House sold in Siesta Isles
18307 Cutlass Dr, Fort Myers Beach, FL 33931
Design your dream waterfront escape in fort myers beach! Imagine waking up every day in a stunning waterfront home that you designed just the way you wanted. Nestled in the highly sought-after siesta isles community, this luxury property is an incredible opportunity for you to finish building your dream home in one of the most prestigious boating communities in southwest florida. With direct sailboat access, you'll be just moments away from endless aquatic adventures, making every day feel like a vacation. As you step onto the property, you'll instantly be captivated by the open concept floor plan and floor to ceiling windowscapes. The outdoor entertainment area is designed to create unforgettable memories. A covered patio beckons you to relax in the shade while enjoying the gentle breeze, and the private swimming pool sparkles invitingly under the warm florida sun. This is the perfect setting for hosting gatherings, or simply unwinding after a long day. Water enthusiasts will revel in the property's exceptional feature, a spacious private dock situated on a sprawling deep-water access canal. This prime docking space accommodates large boats with ease, providing you the freedom to explore the stunning waters of southwest florida at your leisure. Location is everything, and this magnificent estate offers unparalleled access to both the serenity of nature and the vibrancy of local culture. Just minutes away from fort myers beach by car or boat, you'll find yourself immersed in some of the most stunning white sandy beaches in the world. Explore nearby sanibel and captiva islands, where you can indulge in local cuisine, enjoy water sports, or simply bask in the sun. This property is the absence of an hoa, allowing you to have complete freedom over your home without any restrictions. Siesta isles is celebrated as one of the premier deep-water boating communities in the region, facilitating quick access to the gulf of mexico. This waterfront estate in fort myers beach is not just a house; it's a lifestyle choice that encapsulates the very essence of coastal living. With plumbing and framing nearly complete, the canvas is yours to finish according to your desires. Whether you envision a modern paradise or a charming coastal retreat, the options are endless. Don't miss out on this incredible opportunity to make your paradise dream home come true. With the option to build out your custom home with the seller's assistance, your waterfront oasis in one of florida's most coveted locales is within reach. Seize the moment, start crafting the life you've always desired in the heart of southwest florida! Brand new steel roof & brand new pool cage 2025!
Siesta Isles, 18212 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Pending
$1,549,000
  • 3 Beds
  • 2 1/2 Baths
  • 2,186 SqFt
  • $709/SqFt
House for sale in Siesta Isles
18212 Cutlass Dr, Fort Myers Beach, FL 33931
Highly sought after turnkey, waterfront property with a pool is now available and comes fully equipped, offering easy access to the stunning gulf beaches of swfl! Situated in a boating community, this residence lets you enjoy a waterfront lifestyle at your leisure. This home underwent an extensive renovation. Every aspect of this property has been carefully remodeled, featuring numerous enhancements, such as elegant travertine tile, granite countertops, updated bathrooms, custom kitchen installations, a butlers pantry, a wet bar, all-new appliances, a recently installed a/c system, updated electrical and plumbing, a tile roof, and a spacious 3-car garage. Additionally, all windows and sliding doors have electric hurricane shutters for added convenience and safety. Step into outdoor living at its finest on the expansive brick patio, complete with a fully equipped outdoor kitchen featuring two built-in gas grills and a kitchen sink, among other amenities. The property also boasts a large wooden dock with two boat lifts(one 16, 000 pound the other is 10, 000 pounds), offering breathtaking canal views and swift access to the gulf. This unique home stands apart from the rest! Schedule your private showing today!! Owner financing available.
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Siesta Isles, 18403 Deep Passage Ln, Fort Myers Beach, Florida 33931, image 1
Sold - Dec 15, 2023
$1,599,000
  • 4 Beds
  • 4 Baths
  • 3,032 SqFt
  • $527/SqFt
House sold in Siesta Isles
18403 Deep Passage Ln, Fort Myers Beach, FL 33931
We accept backup offers! Concrete block solid built. Discover an extraordinary opportunity to own a gulf-access waterfront haven in fort myers beach. This captivating residence offers direct deep-water access and southern exposure, ensuring your days are bathed in warmth and natural light. With an impressive 120 feet of seawall, this property is a haven for boating enthusiasts. Built in 2003, this 2-story concrete block home spans over 3, 000 square feet and features a well-thought-out design that seamlessly merges indoor and outdoor living. Inside, you'll find 4 spacious bedrooms, 4 full bathrooms, an elevator, impact windows and shutters for added safety, a propane tank, new electrical panels, two brand-new hvac systems, and a recently installed pool pump and a wine cellar. For those with an active lifestyle, a 4-car garage offers ample storage space for recreational gear and vehicles. The two  boat docks are structurally sound, lifts are in good shape. This home was damaged by hurricane ian and was meticulously restored . Located in the hidden gem of a community known as siesta isles, you'll have quick and unobstructed access to the gulf of mexico, without any bridges, making it an ideal location for boating, fishing, and sailing. Enjoy the famous beaches of the world within minutes of your doorstep. Welcome to the epitome of luxury resort living in fort myers beach.
Siesta Isles, 18115 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Sold - Aug 17, 2023
$775,000
  • 0.23 Acres
  • $3,369,565/Acre
Land sold in Siesta Isles
18115 Cutlass Dr, Fort Myers Beach, FL 33931
Located in the exclusive siesta isles boating community, this waterfront property has boating access and is right before the matanzas pass bridge to fort myers beach. The back of the lot over looks a deep water canal leading right out to pelican bay, and fort myers beach. This lot is bare with no grass (grass in pictures digitally staged). The property is capable of having boat dock with its deep water canal and with having direct access to the gulf.
Siesta Isles, 18212 Deep Passage Ln, Fort Myers Beach, Florida 33931, image 1
Sold - Jul 07, 2023
$875,000
  • 3 Beds
  • 2 Baths
  • 1,480 SqFt
  • $591/SqFt
House sold in Siesta Isles
18212 Deep Passage Ln, Fort Myers Beach, FL 33931
Structurally sound in siesta isles!! The most sought after boating community in swfl. Canals are wide, deep and direct. A boaters dream. Bike to the beach and avoid the traffic. This 3 bedroom 2 bath home has been deemed structurally sound by an engineer. Offering beautiful western exposure and a spacious lanai. Plenty of room for your dream pool. The downstairs entrance, utility and storage space add lots of extra room. New 2022 ac condenser matched to the 2017 handler. New dock in 2014, in good condition. Roof 2011 (missing some shingles). Brand new water heater and electrical panel 2022. Note: the home is in its original 1977 condition. No water damage to living area. Don't miss out on this amazing opportunity!
Siesta Isles, 18101 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Sold - May 23, 2023
$1,300,000
  • 3 Beds
  • 3 Baths
  • 2,349 SqFt
  • $553/SqFt
House sold in Siesta Isles
18101 Cutlass Dr, Fort Myers Beach, FL 33931
Incredible opportunity to own a direct gulf access waterfront pool home at fort myers beach! Siesta isles is a hidden gem of a community known for it's wide canals and quick direct (no bridges) access to the gulf of mexico, where you can boat/fish/sail along some of the most famous beaches in the world! Be on the gulf to watch our endless sunsets within minutes! This home was damaged by hurricane ian. Ready and waiting for you to make it your own. Features that are intact include new hurricane impact windows & doors, new tile roof, new electrical panels, new hvac systems (2), new pool pump & heater. Boat dock and canopy is structurally sound, lifts are in good shape, however the motors sustained damage from the salt water. Home has a 500 gallon propane tank buried in the front yard for a generator system, in which the home is wired to accommodate. Book your showing today to see the possibilities!
Siesta Isles, 18600 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Sold - May 08, 2023
$3,800,000
  • 3 Beds
  • 4 Baths
  • 4,866 SqFt
  • $781/SqFt
House sold in Siesta Isles
18600 Cutlass Dr, Fort Myers Beach, FL 33931
Here is a very rare opportunity to purchase one of the most unique properties on ft myers beach. This luxurious estate home was damaged by hurricane ian and current owners no longer wish to rebuild. With almost 200 ft of unrestricted gulf access seawall, it's new owners could park their massive yacht here and still leave room for its amazing view. This home is nestled on a quiet cul-de-sac at the end of cutlass drive offering southern views towards bowditch point and only minutes to the gulf of mexico. With all the convenience of fort myers beach and only a fraction of the traffic makes this property second to none. Starting in 2018 and finishing in 2019 this remarkable home was fully renovated with no expense spared. Currently this home has been remediated from hurricane ian flood waters but will need rebuilding. The current sellers have also included a rendering of another possibility if the new owners wish to start over on this truly amazing location. Ft myers beach and the barrier islands from naples to sanibel are home to some of the most amazing beaches florida has to offer. Don't delay, call your agent today, and make this piece of paradise your next place to stay.
Siesta Isles, 18116 Deep Passage Ln, Fort Myers Beach, Florida 33931, image 1
Sold - Mar 21, 2023
$899,000
  • 3 Beds
  • 2 Baths
  • 1,790 SqFt
  • $502/SqFt
House sold in Siesta Isles
18116 Deep Passage Ln, Fort Myers Beach, FL 33931
Siesta isles is one of the best boating communities in sw florida. Deep water direct access to gulf of mexico. Minutes to open water, no bridges. 2 miles to ft. Myers beach if you want to drive, less than that by boat. Great home fully furnished and sold turnkey. New roof is due in weeks. 2 new air conditioning systems installed last month. Down stairs had damage and ready to be redone to fit your needs. New seawall in august 2016. Large newer dock and lift installed in september 2016. Pool heater and boat lift are not functional due to water damaging the electronics. Home to be sold as is. Main level beautiful and ready to go. If you are looking for income, home is ready to go! Day 1.
Siesta Isles, 18451 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Sold - Mar 13, 2023
$800,000
  • 3 Beds
  • 2 Baths
  • 1,988 SqFt
  • $402/SqFt
House sold in Siesta Isles
18451 Cutlass Dr, Fort Myers Beach, FL 33931
Boaters paradise! Deep-water canal with direct gulf access! This spacious three bedroom/two bath home with florida room, two car garage and work area is located in the coveted siesta isles premier boating community. Parts of this concrete block home sustained damage from hurricane ian, and walls have been mitigated to the studs with on-going clean up. Owner carries flood insurance, the policy is transferable to new owner. Newer 2021 roof. There are three finger docks with six boat slips. The circular drive allows plenty of room for your guest parking and the backyard is perfect for outdoor entertaining or just relaxing while watching the dolphins and other marine life frolic around. Siesta isles is un-incorporated fort myers beach, with white sandy beaches & great local hang-outs right over the bridge, more restaurants, shopping & entrainment on the mainland, salt-water fishing in your backyard and down the canal to the gulf. You're going to love living here with the locals!
Siesta Isles, 18276 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Pending
$3,500,000
  • 6 Beds
  • 6 1/2 Baths
  • 5,767 SqFt
  • $607/SqFt
House for sale in Siesta Isles
18276 Cutlass Dr, Fort Myers Beach, FL 33931
Waterfront living at its best! Welcome to your ultimate fun-filled getaway just minutes from fort myers beach! This 6-bedroom, 7-bathroom canal-front home is designed for making unforgettable memories—whether you're cruising the waterways, hosting poolside parties, or soaking up sun-filled days with the people you love most. The ground level sets the vibe with a custom wrap-around bar—complete with a 12’ shark hanging overhead! Kick back in the theater room or perfect your swing on the indoor golf simulator. The relaxed lounge area flows seamlessly to your private saltwater pool and spa. A tiki hut adds a tropical touch, while the massive sun deck with dining and lounge areas—features a boat lift and large slip for your water toys, so you’re always just moments from your next adventure. The 80' wide canal makes it easy to accommodate most vessels. Take the private elevator up to the second floor, where everyday living meets effortless entertaining. The open-concept layout includes a gourmet kitchen with built-in appliances, a center island cooktop, an oversized breakfast bar, and a spacious eat-in dining area. Exposed beams, a stone accent wall, and a cozy fireplace add warmth and style. Slide open the collapsible glass doors and expand your living space onto a huge balcony overlooking the pool and canal. With a full outdoor kitchen and built-in bbq, it’s the perfect place to grill, gather, and enjoy the coastal breeze. Upstairs, the third floor features three additional bedrooms—including two spacious en-suite rooms and a luxurious primary suite with a spa-like bathroom offering a soaking jet tub and an expansive walk-around shower. But the real showstopper? The private, oversized third-floor balcony, where you’ll enjoy epic panoramic views of the canal, nature preserve, and front-row seats to southwest florida’s jaw-dropping sunsets—a picture-perfect backdrop for peaceful mornings or starlit evenings. Conveniently tucked away from the tourist buzz yet just a short ride to fort myers beach, sanibel island, and cayo costa state park, this home delivers the perfect blend of adventure, comfort, and coastal lifestyle. From boat days and bbq nights to movie marathons and poolside laughs—this is where lifelong memories are made! **be sure to request the cinematic video tour and 3d walk-through!
Siesta Isles, 18548 Cutlass Dr, Fort Myers Beach, Florida 33931, image 1
Pending
$1,450,000 $100K
  • 5 Beds
  • 4 Baths
  • 2,172 SqFt
  • $668/SqFt
House for sale in Siesta Isles
18548 Cutlass Dr, Fort Myers Beach, FL 33931
Discover your dream waterfront estate, your ultimate slice of paradise in the heart of fort myers beach! Nestled within the serene enclave of siesta isles, this stunning property offers a unique opportunity to experience the harmonious blend of opulence and tranquil canal-side living. With breathtaking views, high-end finishes, and an ideal locale, it is a dream come true for those seeking the perfect coastal retreat. As you step through the grand entrance, you'll immediately be captivated by the expansive, bright, and airy spaces that define this majestic estate. The cleverly designed floor plan features floor-to-ceiling windows that flood the interiors with natural light while providing unobstructed views of the picturesque waterfront inviting the beauty of nature indoors. The great room serves as the heart of the home, where you can entertain or simply unwind while soaking in the calming sights of the serene blue waters just beyond. Every inch of this home has been meticulously remodeled to offer modern luxury while maintaining its timeless charm. Equipped with brand new high-end stainless steel appliances and quartz counters, the gourmet kitchen is a culinary enthusiast's dream. Whether you're preparing a casual breakfast or hosting a lavish dinner party, this kitchen seamlessly integrates with the open concept living area, ensuring that you'll never miss a moment with your guests. Stepping outside, the luxurious lifestyle continues. The outdoor area is an entertainer's paradise, featuring a private heated swimming pool and spa surrounded by swaying majestic palms. For the water enthusiasts, the property comes complete with its very own private dock situated on a spacious deep-water access canal. This exceptional feature accommodates large boats, making it easy to embrace the aquatic adventures southwest florida has to offer. The location of this magnificent estate is unparalleled. Situated just minutes away from fort myers beach by car or boat, you'll have easy access to some of the most stunning white sandy beaches and vibrant coastal communities, including sanibel and captiva islands. The neighborhood is brimming with local eateries, lively pubs, and a variety of entertainment options, ensuring that you're always close to fun and excitement. There is no hoa, allowing you the freedom to enjoy your property to the fullest without any restrictions. Siesta isles is recognized as one of the premier deep-water boating communities in southwest florida, offering quick access to the gulf of mexico. You're merely the third lot off the bay, positioning you perfectly to take advantage of all the aquatic adventures the region has to offer. Experience the magic of this tropical oasis where luxury meets tranquility and every day feels like a vacation.
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Streetlight
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Scores

Walk Score®

Car-Dependent. Almost all errands require a car.

7

100

Transit Score®

No data.

N/A

Bike Score®

Somewhat Bikeable. Minimal bike infrastructure.

43

100

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Bearable noise.

80

100

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